3-Iodo-4-methylbenzoic acid → Ethyl 3-iodo-4-methylbenzoate

HRID 1527890Notes

Reaction equation

HRID 1527890 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=[O:6].[C:12](OCC)(=O)[CH3:13].CCCCCC>C(O)C.S(=O)(=O)(O)O>[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([O:7][CH2:12][CH3:13])=[O:6]

Participants

5

Reactant 2

HCID 6216403-Iodo-4-methylbenzoic acidHCID 21226206Ethyl acetate hexane

Product 1

HCID 23073518Ethyl 3-iodo-4-methylbenzoateYield 95%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 3-iodo-4-methylbenzoic acid (1.5 g, 5.7 mmol) in 25 ml of ethanol was dropped in 0.5 ml of concentrated sulfuric acid. The reaction was refluxed overnight. TLC (Ethyl Acetate/Hexane 1:10) indicated the completion of the esterification. The extra ethanol was evaporated and the residue was dissolved in 30 ml of dichloromethane, which was washed with water (10 ml) and brine (10 ml), dried, and evaporated to a thick oil. A white solid was obtained after drying under vacuo (1.56 g, in 95% yield).

Workup

  1. temperatureThe reaction was refluxed overnight
  2. customThe extra ethanol was evaporated
  3. dissolutionthe residue was dissolved in 30 ml of dichloromethane
  4. washwhich was washed with water (10 ml) and brine (10 ml)
  5. customdried
  6. customevaporated to a thick oil
  7. customA white solid was obtained
  8. customafter drying under vacuo (1.56 g, in 95% yield)

Sources & evidence

ORD record
ord-f5b310a012ff4175b02236ce5a9e74e7
Source dataset
uspto-grants-2015_07
Patent number
US09090561B2

Reaction notes

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